This chapter looks at how the extended period of fiscal readjustment has changed the landscape of the prisons system, with new providers, new governance mechanisms, and promises of radical reform. However, no policy sphere operates in isolation, and reforms and cutbacks to important provision in other areas of social policy — particularly housing and social security — have affected the progress of criminal justice reform agendas. Two features of the changing social security landscape over the past decade are worthy of note to set the scene for an exploration of a social security policy targeted at prisoners. The first is a ‘deepening’ and ‘widening’ of the obligation to work, from which only a minority are excused, and the second is a commitment to conditionality, interweaving support with discipline in the form of financial sanctions.